2,2′-[(1S,2S)-1,2-Bis(2-hy­droxy­phen­yl)ethane-1,2-di­yl]bis(isoindoline-1,3-dione) ethanol monosolvate hemihydrate

Chin, J.; Koh, D.; Lough, A.J.

doi:10.1107/S1600536813003978

organic compounds

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ISSN: 2056-9890

Volume 69| Part 3| March 2013| Pages o406-o407

doi:10.1107/S1600536813003978

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2,2′-[(1S,2S)-1,2-Bis(2-hydroxyphenyl)ethane-1,2-diyl]bis(isoindoline-1,3-dione) ethanol monosolvate hemihydrate

Jik Chin,^a Dongsoo Koh ^b and Alan J. Lough ^a ^*

^aDepartment of Chemistry, University of Toronto, Toronto, Ontario, Canada M5S 3H6, and ^bDepartment of Applied Chemistry, Dongduk Women's University, Seoul 136-714, Republic of Korea
^*Correspondence e-mail: alough@chem.utoronto.ca

(Received 13 December 2012; accepted 8 February 2013; online 20 February 2013)

In the title compound, C₃₀H₂₀N₂O₆·C₂H₆O·0.5H₂O, the solvent water molecule lies on a twofold rotation axis. The dihedral angle between the essentially planar isoindole ring systems [maximum deviations = 0.028 (1) and 0.022 (1) Å] is 47.12 (5)°. The dihedral angle between the benzene rings is 81.32 (7)°. In the crystal, the components are linked into a three-dimensional network via O—H⋯O hydrogen bonds.

Related literature

For the use of chiral bisphenolic ligands in stereoselective catalysis, see: Noyori et al. (1984 ); Takaya et al. (1989 ); Liu & Ding (2005 ); Xu et al. (2011 ); Yamaguchi et al. (2009 ); Van den Berg et al. (2002 ); So et al. (2012 ); Kim, Nguyen et al. (2008 ); Kim, So et al. (2008 ); For related structures, see: Li et al. (2011 ); Liu et al. (2011 ). For analysis of the absolute configration, see: Hooft et al. (2008 ).

Experimental

Crystal data

C₃₀H₂₀N₂O₆·C₂H₆O·0.5H₂O
M_r = 559.56
Tetragonal, P 4₁ 2₁ 2
a = 10.6848 (3) Å
c = 47.9935 (17) Å
V = 5479.2 (3) Å³
Z = 8
Cu Kα radiation
μ = 0.81 mm⁻¹
T = 147 K
0.29 × 0.18 × 0.18 mm

Data collection

Bruker Kappa APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.696, T_max = 0.753
35250 measured reflections
4786 independent reflections
4756 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.075
S = 1.12
4786 reflections
391 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.18 e Å⁻³
Absolute structure: Flack (1983 ), 1895 Friedel pairs
Flack parameter: 0.03 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O1W	0.86 (2)	1.89 (2)	2.7263 (13)	165 (2)
O2—H2O⋯O5ⁱ	0.88 (2)	1.95 (2)	2.8238 (15)	177 (2)
O1S—H1SO⋯O4	1.06 (4)	1.76 (4)	2.7905 (17)	161 (3)
O1W—H1W⋯O1Sⁱⁱ	1.06 (3)	1.65 (3)	2.6927 (16)	169 (3)
Symmetry codes: (i) $[-x-{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 4}}]$ ; (ii) x, y+1, z.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813003978/aa2082sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813003978/aa2082Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813003978/aa2082Isup3.cml

checkCIF report

Comment top

Binol (1, see Fig. 1) is a privileged structure for developing a wide variety of stereoselective catalysts (Noyori et al., 1984; Takaya et al., 1989). More recently, other chiral bisphenolic compounds (2, 3) have also gained popularity (Liu & Ding, 2005; Xu et al., 2011). The phenolic O atoms in these compounds are useful for chelating to metals (Yamaguchi et al., 2009) or for forming monophos ligands (Van den Berg et al., 2002). We have shown that bis-(2-hydroxyphenyl)-1,2-diaminoethane (hpen) is a highly useful chiral diamine for making many other chiral diamines by diaza-Cope rearrangement (So et al., 2012; Kim, Nguyen et al., 2008; Kim, So et al., 2008). Here we report a structure of a chiral bisphenolic compound (4) derived from hpen by simple protection of the amino groups as phthalimides (Li et al., 2011; Liu et al., 2011). As anticipated from molecular mechanics computation, the structure reveals that the two phenol groups in 4 are in a gauche arrangement.

The molecular structure of the title compound (4) is shown in Fig. 2. The solvent water molecule lies on a twofold rotation axis. The dihedral angle between the essentially planar isoindole ring systems [N1/C15—C22 and N2/C23—C30, with maximum deviations of 0.028 (1) for C15 and 0.022 (1) Å for C24) is 47.12 (5)°. The dihedral angle between the two benzene rings [C3—C8 and C9—C14 is 81.32 (7)°]. In the crystal, the components of the structure are linked into a three-dimensional network via O—H···O hydrogen bonds (Fig. 3).

Related literature top

For the use of chiral bisphenolic ligands in stereoselective catalysis, see: Noyori et al. (1984); Takaya et al. (1989); Liu & Ding (2005); Xu et al. (2011); Yamaguchi et al. (2009); Van den Berg et al. (2002); So et al. (2012); Kim, Nguyen et al. (2008); Kim, So et al. (2008); For related structures, see: Li et al. (2011); Liu et al. (2011). For analysis of the absolute configration, see: Hooft et al. (2008).

Experimental top

To a suspension of phthalic anhydride (1.48 g, 10 mmol) in 10 ml of acetic acid was added 1,2-bis(2-hydroxyphenyl)-1,2-diaminoethane (1.22 g, 5 mmol). The reaction mixture was heated at 383 K for 16 h and cooled down to room temperature to give the product as off white precipitate. After filtration, recrystallization of the title compound in ethanol gave X-ray quality crystals in 58% yield (1.47 g).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Chiral bisphenolic ligands used for stereoselective catalysis.
	Fig. 2. The molecular structure of the title compound with 30% probability ellipsoids. The ethanol solvent molecule and hemihydrate are not shown.
	Fig. 3. Part of the crystal structure with hydrogen bonds shown as dashed lines.

2,2'-[(1S,2S)-1,2-Bis(2-hydroxyphenyl)ethane-1,2-diyl]bis(isoindoline-1,3-dione) ethanol monosolvate hemihydrate top

Crystal data top

C₃₀H₂₀N₂O₆·C₂H₆O·0.5H₂O	D_x = 1.357 Mg m⁻³
M_r = 559.56	Cu Kα radiation, λ = 1.54178 Å
Tetragonal, P4₁2₁2	Cell parameters from 9692 reflections
Hall symbol: P 4abw 2nw	θ = 3.7–66.5°
a = 10.6848 (3) Å	µ = 0.81 mm⁻¹
c = 47.9935 (17) Å	T = 147 K
V = 5479.2 (3) Å³	Needle, pale yellow
Z = 8	0.29 × 0.18 × 0.18 mm
F(000) = 2344

Data collection top

Bruker Kappa APEX DUO CCD diffractometer	4786 independent reflections
Radiation source: Bruker ImuS	4756 reflections with I > 2σ(I)
Multi-layer optics monochromator	R_int = 0.035
ϕ and ω scans	θ_max = 66.6°, θ_min = 3.7°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −11→12
T_min = 0.696, T_max = 0.753	k = −12→12
35250 measured reflections	l = −53→56

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.075	w = 1/[σ²(F_o²) + (0.0389P)² + 1.2163P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max = 0.001
4786 reflections	Δρ_max = 0.26 e Å⁻³
391 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1895 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.03 (13)

Crystal data top

C₃₀H₂₀N₂O₆·C₂H₆O·0.5H₂O	Z = 8
M_r = 559.56	Cu Kα radiation
Tetragonal, P4₁2₁2	µ = 0.81 mm⁻¹
a = 10.6848 (3) Å	T = 147 K
c = 47.9935 (17) Å	0.29 × 0.18 × 0.18 mm
V = 5479.2 (3) Å³

Data collection top

Bruker Kappa APEX DUO CCD diffractometer	4786 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	4756 reflections with I > 2σ(I)
T_min = 0.696, T_max = 0.753	R_int = 0.035
35250 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.075	Δρ_max = 0.26 e Å⁻³
S = 1.12	Δρ_min = −0.18 e Å⁻³
4786 reflections	Absolute structure: Flack (1983), 1895 Friedel pairs
391 parameters	Absolute structure parameter: 0.03 (13)
0 restraints

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	−0.12757 (12)	0.57392 (11)	0.02270 (2)	0.0380 (3)
O2	−0.27045 (11)	0.13393 (10)	0.10646 (2)	0.0335 (3)
O3	0.16202 (10)	0.49860 (10)	0.05562 (2)	0.0337 (3)
O4	0.03625 (10)	0.10133 (9)	0.03340 (2)	0.0285 (2)
O5	−0.05120 (10)	0.50131 (9)	0.11171 (2)	0.0276 (2)
O6	0.05013 (10)	0.09166 (9)	0.09551 (2)	0.0295 (2)
N1	0.06521 (10)	0.31129 (11)	0.04480 (2)	0.0198 (2)
N2	−0.02832 (11)	0.29340 (11)	0.09907 (2)	0.0206 (2)
C1	−0.06345 (12)	0.35618 (13)	0.05051 (3)	0.0202 (3)
H1A	−0.0559	0.4460	0.0561	0.024*
C2	−0.11822 (12)	0.28568 (13)	0.07582 (3)	0.0201 (3)
H2A	−0.1259	0.1955	0.0705	0.024*
C3	−0.14501 (13)	0.35352 (14)	0.02451 (3)	0.0232 (3)
C4	−0.19143 (13)	0.24298 (15)	0.01311 (3)	0.0264 (3)
H4A	−0.1747	0.1657	0.0222	0.032*
C5	−0.26174 (15)	0.24368 (17)	−0.01123 (3)	0.0336 (4)
H5A	−0.2908	0.1673	−0.0190	0.040*
C6	−0.28897 (16)	0.35578 (18)	−0.02399 (3)	0.0371 (4)
H6A	−0.3377	0.3567	−0.0405	0.045*
C7	−0.24576 (17)	0.46746 (17)	−0.01282 (3)	0.0365 (4)
H7A	−0.2656	0.5446	−0.0216	0.044*
C8	−0.17327 (15)	0.46656 (15)	0.01131 (3)	0.0288 (3)
C9	−0.24683 (13)	0.33031 (13)	0.08481 (3)	0.0212 (3)
C10	−0.29333 (14)	0.44909 (14)	0.07941 (3)	0.0249 (3)
H10A	−0.2441	0.5064	0.0690	0.030*
C11	−0.41034 (14)	0.48579 (14)	0.08892 (3)	0.0284 (3)
H11A	−0.4406	0.5676	0.0851	0.034*
C12	−0.48290 (14)	0.40203 (15)	0.10405 (3)	0.0290 (3)
H12A	−0.5633	0.4264	0.1105	0.035*
C13	−0.43858 (14)	0.28366 (15)	0.10968 (3)	0.0285 (3)
H13A	−0.4887	0.2263	0.1199	0.034*
C14	−0.32052 (14)	0.24807 (14)	0.10041 (3)	0.0248 (3)
C15	0.16844 (13)	0.39132 (13)	0.04779 (3)	0.0230 (3)
C16	0.28018 (13)	0.31660 (14)	0.04040 (3)	0.0237 (3)
C17	0.40449 (15)	0.35044 (16)	0.03946 (3)	0.0331 (4)
H17A	0.4304	0.4338	0.0432	0.040*
C18	0.49035 (15)	0.25736 (19)	0.03282 (4)	0.0397 (4)
H18A	0.5770	0.2772	0.0322	0.048*
C19	0.45225 (15)	0.13664 (18)	0.02712 (3)	0.0367 (4)
H19A	0.5133	0.0752	0.0227	0.044*
C20	0.32610 (15)	0.10254 (15)	0.02776 (3)	0.0281 (3)
H20A	0.2997	0.0196	0.0237	0.034*
C21	0.24159 (13)	0.19577 (14)	0.03461 (3)	0.0218 (3)
C22	0.10333 (13)	0.19047 (13)	0.03709 (3)	0.0208 (3)
C23	−0.00112 (13)	0.40013 (13)	0.11452 (3)	0.0210 (3)
C24	0.10131 (13)	0.36512 (13)	0.13406 (3)	0.0229 (3)
C25	0.16348 (15)	0.43582 (14)	0.15371 (3)	0.0273 (3)
H25A	0.1404	0.5201	0.1573	0.033*
C26	0.26124 (16)	0.37874 (15)	0.16801 (3)	0.0305 (3)
H26A	0.3067	0.4254	0.1815	0.037*
C27	0.29385 (14)	0.25485 (15)	0.16298 (3)	0.0289 (3)
H27A	0.3613	0.2184	0.1730	0.035*
C28	0.22891 (14)	0.18341 (15)	0.14344 (3)	0.0269 (3)
H28A	0.2497	0.0982	0.1402	0.032*
C29	0.13328 (13)	0.24133 (13)	0.12906 (3)	0.0229 (3)
C30	0.05112 (13)	0.19354 (13)	0.10641 (3)	0.0225 (3)
O1S	−0.15257 (14)	−0.07024 (14)	0.04583 (3)	0.0540 (4)
C1S	−0.1589 (2)	−0.1315 (2)	0.07221 (4)	0.0479 (5)
H1SA	−0.1368	−0.0721	0.0872	0.057*
H1SB	−0.0987	−0.2020	0.0727	0.057*
C2S	−0.2877 (2)	−0.1788 (2)	0.07646 (4)	0.0545 (5)
H2SA	−0.2932	−0.2205	0.0946	0.082*
H2SB	−0.3085	−0.2386	0.0617	0.082*
H2SC	−0.3467	−0.1087	0.0759	0.082*
O1W	−0.20559 (11)	0.79441 (11)	0.0000	0.0348 (4)
H1O	−0.153 (2)	0.636 (2)	0.0128 (5)	0.052 (6)*
H2O	−0.324 (2)	0.093 (2)	0.1168 (4)	0.046 (6)*
H1SO	−0.068 (3)	−0.019 (3)	0.0430 (7)	0.111 (11)*
H1W	−0.178 (3)	0.853 (3)	0.0165 (6)	0.095 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0515 (7)	0.0252 (6)	0.0372 (6)	0.0009 (5)	−0.0126 (5)	0.0079 (5)
O2	0.0345 (6)	0.0240 (5)	0.0420 (6)	0.0025 (5)	0.0136 (5)	0.0098 (5)
O3	0.0308 (6)	0.0229 (5)	0.0475 (6)	−0.0061 (5)	0.0054 (5)	−0.0099 (5)
O4	0.0265 (5)	0.0237 (5)	0.0352 (6)	−0.0050 (4)	0.0041 (4)	−0.0052 (4)
O5	0.0318 (5)	0.0214 (5)	0.0297 (5)	0.0065 (4)	0.0021 (4)	−0.0017 (4)
O6	0.0371 (6)	0.0197 (5)	0.0316 (5)	0.0062 (4)	−0.0032 (5)	−0.0038 (4)
N1	0.0175 (6)	0.0203 (6)	0.0215 (5)	−0.0006 (4)	0.0016 (4)	−0.0012 (5)
N2	0.0233 (6)	0.0192 (6)	0.0195 (5)	0.0015 (5)	0.0010 (5)	−0.0009 (4)
C1	0.0182 (6)	0.0199 (7)	0.0224 (6)	0.0005 (5)	0.0030 (5)	0.0008 (5)
C2	0.0208 (7)	0.0195 (7)	0.0201 (6)	−0.0001 (5)	0.0020 (5)	−0.0009 (5)
C3	0.0189 (6)	0.0292 (7)	0.0214 (7)	0.0014 (6)	0.0037 (5)	0.0007 (6)
C4	0.0204 (7)	0.0315 (8)	0.0271 (7)	−0.0018 (6)	0.0035 (6)	−0.0016 (6)
C5	0.0251 (8)	0.0449 (9)	0.0307 (8)	−0.0020 (7)	−0.0015 (6)	−0.0087 (7)
C6	0.0294 (8)	0.0562 (11)	0.0257 (8)	0.0048 (8)	−0.0051 (6)	−0.0040 (7)
C7	0.0395 (9)	0.0432 (9)	0.0268 (7)	0.0073 (7)	−0.0034 (7)	0.0067 (7)
C8	0.0283 (8)	0.0326 (8)	0.0254 (7)	0.0010 (6)	0.0021 (6)	0.0014 (6)
C9	0.0200 (7)	0.0232 (7)	0.0204 (6)	−0.0008 (5)	0.0018 (5)	−0.0021 (5)
C10	0.0247 (7)	0.0235 (7)	0.0265 (7)	−0.0008 (6)	0.0028 (6)	0.0004 (6)
C11	0.0255 (7)	0.0261 (7)	0.0336 (8)	0.0060 (6)	0.0006 (6)	−0.0020 (6)
C12	0.0214 (7)	0.0344 (8)	0.0312 (8)	0.0009 (6)	0.0055 (6)	−0.0051 (6)
C13	0.0257 (7)	0.0306 (8)	0.0291 (7)	−0.0030 (6)	0.0080 (6)	0.0010 (6)
C14	0.0269 (7)	0.0238 (7)	0.0238 (7)	−0.0003 (6)	0.0038 (6)	−0.0006 (6)
C15	0.0238 (7)	0.0237 (7)	0.0215 (7)	−0.0039 (6)	0.0024 (5)	0.0005 (6)
C16	0.0211 (7)	0.0297 (7)	0.0204 (6)	−0.0025 (6)	0.0014 (5)	0.0000 (6)
C17	0.0235 (8)	0.0395 (9)	0.0364 (8)	−0.0064 (6)	0.0008 (6)	−0.0073 (7)
C18	0.0204 (7)	0.0592 (11)	0.0396 (9)	−0.0008 (7)	0.0015 (7)	−0.0090 (8)
C19	0.0258 (8)	0.0504 (10)	0.0340 (8)	0.0102 (8)	0.0022 (7)	−0.0047 (7)
C20	0.0293 (8)	0.0325 (8)	0.0224 (7)	0.0061 (6)	0.0009 (6)	−0.0020 (6)
C21	0.0212 (7)	0.0278 (7)	0.0163 (6)	0.0004 (6)	0.0006 (5)	0.0005 (5)
C22	0.0216 (7)	0.0223 (7)	0.0186 (6)	0.0010 (6)	0.0021 (5)	0.0011 (5)
C23	0.0233 (7)	0.0208 (7)	0.0188 (6)	−0.0004 (5)	0.0055 (5)	−0.0006 (5)
C24	0.0263 (7)	0.0221 (7)	0.0204 (6)	0.0000 (6)	0.0043 (6)	0.0016 (6)
C25	0.0328 (8)	0.0248 (7)	0.0245 (7)	−0.0027 (6)	0.0020 (6)	0.0004 (6)
C26	0.0343 (8)	0.0327 (8)	0.0246 (7)	−0.0109 (7)	−0.0022 (6)	0.0018 (6)
C27	0.0259 (7)	0.0333 (8)	0.0275 (7)	−0.0028 (6)	−0.0004 (6)	0.0075 (6)
C28	0.0276 (8)	0.0266 (7)	0.0266 (7)	0.0024 (6)	0.0021 (6)	0.0041 (6)
C29	0.0227 (7)	0.0242 (7)	0.0218 (7)	0.0011 (6)	0.0034 (5)	0.0010 (6)
C30	0.0232 (7)	0.0221 (7)	0.0223 (6)	0.0020 (6)	0.0042 (5)	0.0011 (6)
O1S	0.0582 (9)	0.0541 (8)	0.0497 (8)	−0.0259 (7)	−0.0012 (7)	0.0048 (7)
C1S	0.0512 (11)	0.0473 (11)	0.0453 (10)	−0.0082 (9)	−0.0092 (9)	0.0008 (8)
C2S	0.0588 (13)	0.0618 (13)	0.0430 (10)	−0.0186 (10)	−0.0028 (9)	0.0056 (9)
O1W	0.0324 (5)	0.0324 (5)	0.0394 (9)	−0.0010 (7)	−0.0075 (5)	0.0075 (5)

Geometric parameters (Å, º) top

O1—C8	1.361 (2)	C12—H12A	0.9500
O1—H1O	0.86 (2)	C13—C14	1.391 (2)
O2—C14	1.3630 (19)	C13—H13A	0.9500
O2—H2O	0.88 (2)	C15—C16	1.479 (2)
O3—C15	1.2082 (18)	C16—C17	1.377 (2)
O4—C22	1.2050 (18)	C16—C21	1.383 (2)
O5—C23	1.2137 (17)	C17—C18	1.390 (2)
O6—C30	1.2078 (18)	C17—H17A	0.9500
N1—C15	1.4030 (18)	C18—C19	1.380 (3)
N1—C22	1.4033 (18)	C18—H18A	0.9500
N1—C1	1.4815 (17)	C19—C20	1.397 (2)
N2—C23	1.3909 (18)	C19—H19A	0.9500
N2—C30	1.4081 (18)	C20—C21	1.384 (2)
N2—C2	1.4749 (18)	C20—H20A	0.9500
C1—C3	1.5222 (19)	C21—C22	1.4832 (19)
C1—C2	1.5444 (18)	C23—C24	1.489 (2)
C1—H1A	1.0000	C24—C25	1.379 (2)
C2—C9	1.5173 (19)	C24—C29	1.387 (2)
C2—H2A	1.0000	C25—C26	1.391 (2)
C3—C4	1.393 (2)	C25—H25A	0.9500
C3—C8	1.397 (2)	C26—C27	1.390 (2)
C4—C5	1.389 (2)	C26—H26A	0.9500
C4—H4A	0.9500	C27—C28	1.394 (2)
C5—C6	1.376 (3)	C27—H27A	0.9500
C5—H5A	0.9500	C28—C29	1.380 (2)
C6—C7	1.387 (3)	C28—H28A	0.9500
C6—H6A	0.9500	C29—C30	1.488 (2)
C7—C8	1.393 (2)	O1S—C1S	1.427 (2)
C7—H7A	0.9500	O1S—H1SO	1.06 (4)
C9—C10	1.387 (2)	C1S—C2S	1.481 (3)
C9—C14	1.397 (2)	C1S—H1SA	0.9900
C10—C11	1.388 (2)	C1S—H1SB	0.9900
C10—H10A	0.9500	C2S—H2SA	0.9800
C11—C12	1.389 (2)	C2S—H2SB	0.9800
C11—H11A	0.9500	C2S—H2SC	0.9800
C12—C13	1.377 (2)	O1W—H1W	1.06 (3)

C8—O1—H1O	108.3 (15)	C17—C16—C21	121.72 (14)
C14—O2—H2O	108.4 (14)	C17—C16—C15	130.12 (14)
C15—N1—C22	111.07 (11)	C21—C16—C15	108.13 (12)
C15—N1—C1	120.88 (11)	C16—C17—C18	117.14 (16)
C22—N1—C1	128.01 (11)	C16—C17—H17A	121.4
C23—N2—C30	111.23 (11)	C18—C17—H17A	121.4
C23—N2—C2	125.82 (11)	C19—C18—C17	121.30 (16)
C30—N2—C2	122.64 (11)	C19—C18—H18A	119.4
N1—C1—C3	111.94 (11)	C17—C18—H18A	119.4
N1—C1—C2	109.82 (11)	C18—C19—C20	121.61 (15)
C3—C1—C2	114.75 (11)	C18—C19—H19A	119.2
N1—C1—H1A	106.6	C20—C19—H19A	119.2
C3—C1—H1A	106.6	C21—C20—C19	116.56 (15)
C2—C1—H1A	106.6	C21—C20—H20A	121.7
N2—C2—C9	110.91 (10)	C19—C20—H20A	121.7
N2—C2—C1	108.73 (11)	C16—C21—C20	121.66 (14)
C9—C2—C1	114.44 (11)	C16—C21—C22	108.45 (13)
N2—C2—H2A	107.5	C20—C21—C22	129.89 (14)
C9—C2—H2A	107.5	O4—C22—N1	126.39 (12)
C1—C2—H2A	107.5	O4—C22—C21	127.65 (13)
C4—C3—C8	118.56 (13)	N1—C22—C21	105.96 (12)
C4—C3—C1	122.80 (13)	O5—C23—N2	125.38 (13)
C8—C3—C1	118.64 (13)	O5—C23—C24	128.16 (13)
C5—C4—C3	121.22 (15)	N2—C23—C24	106.45 (11)
C5—C4—H4A	119.4	C25—C24—C29	121.47 (14)
C3—C4—H4A	119.4	C25—C24—C23	130.33 (13)
C6—C5—C4	119.56 (15)	C29—C24—C23	108.16 (12)
C6—C5—H5A	120.2	C24—C25—C26	117.33 (14)
C4—C5—H5A	120.2	C24—C25—H25A	121.3
C5—C6—C7	120.41 (14)	C26—C25—H25A	121.3
C5—C6—H6A	119.8	C27—C26—C25	121.36 (14)
C7—C6—H6A	119.8	C27—C26—H26A	119.3
C6—C7—C8	120.02 (16)	C25—C26—H26A	119.3
C6—C7—H7A	120.0	C26—C27—C28	120.89 (14)
C8—C7—H7A	120.0	C26—C27—H27A	119.6
O1—C8—C7	121.83 (14)	C28—C27—H27A	119.6
O1—C8—C3	117.96 (13)	C29—C28—C27	117.36 (14)
C7—C8—C3	120.21 (15)	C29—C28—H28A	121.3
C10—C9—C14	118.27 (13)	C27—C28—H28A	121.3
C10—C9—C2	123.96 (12)	C28—C29—C24	121.58 (14)
C14—C9—C2	117.72 (12)	C28—C29—C30	130.44 (13)
C9—C10—C11	121.31 (13)	C24—C29—C30	107.96 (12)
C9—C10—H10A	119.3	O6—C30—N2	124.71 (13)
C11—C10—H10A	119.3	O6—C30—C29	129.13 (13)
C10—C11—C12	119.53 (14)	N2—C30—C29	106.16 (12)
C10—C11—H11A	120.2	C1S—O1S—H1SO	112.9 (17)
C12—C11—H11A	120.2	O1S—C1S—C2S	108.83 (16)
C13—C12—C11	120.16 (14)	O1S—C1S—H1SA	109.9
C13—C12—H12A	119.9	C2S—C1S—H1SA	109.9
C11—C12—H12A	119.9	O1S—C1S—H1SB	109.9
C12—C13—C14	120.01 (14)	C2S—C1S—H1SB	109.9
C12—C13—H13A	120.0	H1SA—C1S—H1SB	108.3
C14—C13—H13A	120.0	C1S—C2S—H2SA	109.5
O2—C14—C13	122.18 (13)	C1S—C2S—H2SB	109.5
O2—C14—C9	117.10 (13)	H2SA—C2S—H2SB	109.5
C13—C14—C9	120.71 (14)	C1S—C2S—H2SC	109.5
O3—C15—N1	124.43 (14)	H2SA—C2S—H2SC	109.5
O3—C15—C16	129.23 (13)	H2SB—C2S—H2SC	109.5
N1—C15—C16	106.32 (11)

C15—N1—C1—C3	116.36 (13)	O3—C15—C16—C21	175.63 (15)
C22—N1—C1—C3	−65.99 (17)	N1—C15—C16—C21	−2.64 (15)
C15—N1—C1—C2	−114.96 (13)	C21—C16—C17—C18	−0.9 (2)
C22—N1—C1—C2	62.69 (17)	C15—C16—C17—C18	177.31 (15)
C23—N2—C2—C9	−55.50 (17)	C16—C17—C18—C19	0.7 (3)
C30—N2—C2—C9	131.43 (13)	C17—C18—C19—C20	0.0 (3)
C23—N2—C2—C1	71.16 (16)	C18—C19—C20—C21	−0.5 (2)
C30—N2—C2—C1	−101.91 (14)	C17—C16—C21—C20	0.4 (2)
N1—C1—C2—N2	51.45 (13)	C15—C16—C21—C20	−178.14 (12)
C3—C1—C2—N2	178.57 (11)	C17—C16—C21—C22	−179.33 (14)
N1—C1—C2—C9	176.06 (10)	C15—C16—C21—C22	2.09 (15)
C3—C1—C2—C9	−56.82 (15)	C19—C20—C21—C16	0.3 (2)
N1—C1—C3—C4	73.68 (16)	C19—C20—C21—C22	180.00 (15)
C2—C1—C3—C4	−52.35 (18)	C15—N1—C22—O4	178.83 (13)
N1—C1—C3—C8	−105.50 (14)	C1—N1—C22—O4	1.0 (2)
C2—C1—C3—C8	128.47 (14)	C15—N1—C22—C21	−0.94 (15)
C8—C3—C4—C5	1.6 (2)	C1—N1—C22—C21	−178.78 (12)
C1—C3—C4—C5	−177.58 (13)	C16—C21—C22—O4	179.46 (14)
C3—C4—C5—C6	−1.7 (2)	C20—C21—C22—O4	−0.3 (2)
C4—C5—C6—C7	0.6 (2)	C16—C21—C22—N1	−0.78 (15)
C5—C6—C7—C8	0.6 (2)	C20—C21—C22—N1	179.48 (14)
C6—C7—C8—O1	179.03 (15)	C30—N2—C23—O5	176.69 (13)
C6—C7—C8—C3	−0.7 (2)	C2—N2—C23—O5	3.0 (2)
C4—C3—C8—O1	179.85 (13)	C30—N2—C23—C24	−1.99 (15)
C1—C3—C8—O1	−0.9 (2)	C2—N2—C23—C24	−175.74 (11)
C4—C3—C8—C7	−0.4 (2)	O5—C23—C24—C25	0.8 (2)
C1—C3—C8—C7	178.83 (14)	N2—C23—C24—C25	179.41 (14)
N2—C2—C9—C10	99.23 (15)	O5—C23—C24—C29	−177.04 (13)
C1—C2—C9—C10	−24.22 (18)	N2—C23—C24—C29	1.60 (15)
N2—C2—C9—C14	−78.18 (15)	C29—C24—C25—C26	1.1 (2)
C1—C2—C9—C14	158.37 (13)	C23—C24—C25—C26	−176.41 (14)
C14—C9—C10—C11	−0.6 (2)	C24—C25—C26—C27	−0.9 (2)
C2—C9—C10—C11	−177.99 (13)	C25—C26—C27—C28	−0.3 (2)
C9—C10—C11—C12	−0.3 (2)	C26—C27—C28—C29	1.2 (2)
C10—C11—C12—C13	0.4 (2)	C27—C28—C29—C24	−1.0 (2)
C11—C12—C13—C14	0.5 (2)	C27—C28—C29—C30	177.11 (14)
C12—C13—C14—O2	177.19 (14)	C25—C24—C29—C28	−0.2 (2)
C12—C13—C14—C9	−1.4 (2)	C23—C24—C29—C28	177.82 (13)
C10—C9—C14—O2	−177.22 (13)	C25—C24—C29—C30	−178.67 (13)
C2—C9—C14—O2	0.34 (19)	C23—C24—C29—C30	−0.63 (15)
C10—C9—C14—C13	1.5 (2)	C23—N2—C30—O6	−177.39 (13)
C2—C9—C14—C13	179.05 (13)	C2—N2—C30—O6	−3.4 (2)
C22—N1—C15—O3	−176.19 (14)	C23—N2—C30—C29	1.62 (15)
C1—N1—C15—O3	1.8 (2)	C2—N2—C30—C29	175.60 (11)
C22—N1—C15—C16	2.18 (15)	C28—C29—C30—O6	0.1 (3)
C1—N1—C15—C16	−179.80 (11)	C24—C29—C30—O6	178.40 (14)
O3—C15—C16—C17	−2.8 (3)	C28—C29—C30—N2	−178.82 (14)
N1—C15—C16—C17	178.95 (15)	C24—C29—C30—N2	−0.55 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O1W	0.86 (2)	1.89 (2)	2.7263 (13)	165 (2)
O2—H2O···O5ⁱ	0.88 (2)	1.95 (2)	2.8238 (15)	177 (2)
O1S—H1SO···O4	1.06 (4)	1.76 (4)	2.7905 (17)	161 (3)
O1W—H1W···O1Sⁱⁱ	1.06 (3)	1.65 (3)	2.6927 (16)	169 (3)

Symmetry codes: (i) −x−1/2, y−1/2, −z+1/4; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₃₀H₂₀N₂O₆·C₂H₆O·0.5H₂O
M_r	559.56
Crystal system, space group	Tetragonal, P4₁2₁2
Temperature (K)	147
a, c (Å)	10.6848 (3), 47.9935 (17)
V (Å³)	5479.2 (3)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	0.81
Crystal size (mm)	0.29 × 0.18 × 0.18

Data collection
Diffractometer	Bruker Kappa APEX DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.696, 0.753
No. of measured, independent and observed [I > 2σ(I)] reflections	35250, 4786, 4756
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.075, 1.12
No. of reflections	4786
No. of parameters	391
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.18
Absolute structure	Flack (1983), 1895 Friedel pairs
Absolute structure parameter	0.03 (13)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O1W	0.86 (2)	1.89 (2)	2.7263 (13)	165 (2)
O2—H2O···O5ⁱ	0.88 (2)	1.95 (2)	2.8238 (15)	177 (2)
O1S—H1SO···O4	1.06 (4)	1.76 (4)	2.7905 (17)	161 (3)
O1W—H1W···O1Sⁱⁱ	1.06 (3)	1.65 (3)	2.6927 (16)	169 (3)

Symmetry codes: (i) −x−1/2, y−1/2, −z+1/4; (ii) x, y+1, z.

Acknowledgements

Financial support of this research by the NSERC is gratefully acknowledged. DK gratefully acknowledges the sabbatical program of Dongduk Womens University. The University of Toronto thanks the NSERC Canada for funding.

References

Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Hooft, R. W. W., Straver, L. H. & Spek, A. L. (2008). J. Appl. Cryst. 41, 96–103. Web of Science CrossRef CAS IUCr Journals Google Scholar
Kim, H., Nguyen, Y., Yen, C. P.-H., Chagal, L., Lough, A. J., Kim, B. M. & Chin, J. (2008). J. Am. Chem. Soc. 130, 12184–12191. Web of Science CrossRef PubMed CAS Google Scholar
Kim, H., So, S. M., Chin, J. & Kim, B. M. (2008). Aldrichim. Acta, 41, 77–88. Google Scholar
Li, C., Fu, X.-K., Wu, C.-L. & Huang, J. (2011). Acta Cryst. E67, o1483. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liu, Y. & Ding, K. (2005). J. Am. Chem. Soc. 127, 10488–10489. Web of Science CSD CrossRef PubMed CAS Google Scholar
Liu, Z.-J., Fu, X.-K., Hu, Z.-K., Wu, X.-J. & Wu, L. (2011). Acta Cryst. E67, o1562. Web of Science CSD CrossRef IUCr Journals Google Scholar
Noyori, R., Tomino, I., Tanimoto, Y. & Nishizawa, M. (1984). J. Am. Chem. Soc. 106, 6709–6716. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
So, S. M., Mui, L., Kim, H. & Chin, J. (2012). Acc. Chem. Res. 45, 1345–1355. Web of Science CrossRef CAS PubMed Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Takaya, H., Akutagawa, S. & Noyori, R. (1989). Org. Synth. 67, 20–32. CAS Google Scholar
Van den Berg, M., Haak, R. M., Minnaard, A. J., De Vries, A. H. M., De Vries, J. G. & Feringa, B. L. (2002). Adv. Synth. Catal. 344, 1003–1007. CAS Google Scholar
Xu, B., Zhu, S.-F., Xie, X.-L., Shen, J.-J. & Zhou, Q.-L. (2011). Angew. Chem. Int. Ed. Engl. 50, 11483–11486. Web of Science CrossRef CAS PubMed Google Scholar
Yamaguchi, A., Matsunaga, S. & Shibasaki, M. (2009). J. Am. Chem. Soc. 131, 10842–10843. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 69| Part 3| March 2013| Pages o406-o407

doi:10.1107/S1600536813003978

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2,2′-[(1S,2S)-1,2-Bis(2-hy­dr­oxy­phen­yl)ethane-1,2-di­yl]bis­(isoindoline-1,3-dione) ethanol monosolvate hemihydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2,2′-[(1S,2S)-1,2-Bis(2-hydroxyphenyl)ethane-1,2-diyl]bis(isoindoline-1,3-dione) ethanol monosolvate hemihydrate